TN-14003 | CAS#368874-31-1 | anti-tumor

MedKoo Cat#: 585250 | Name: TN-14003

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TN-14003 is a synthetic antagonist 14-mer peptide inhibiting metastasis in an animal model.

Chemical Structure

TN-14003

CAS#368874-31-1

Theoretical Analysis

MedKoo Cat#: 585250

Name: TN-14003

CAS#: 368874-31-1

Chemical Formula: C90H141N33O18S2

Exact Mass: 2036.0574

Molecular Weight: 2037.45

Elemental Analysis: C, 53.06; H, 6.98; N, 22.69; O, 14.13; S, 3.15

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

TN-14003; TN14003; TN 14003

IUPAC/Chemical Name

(3R,6S,9S,12S,15R,20R,23S,26S,29S,32S)-3,6-bis(4-aminobutyl)-N-[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]-15-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]-26-(3-carbamimidamidopropyl)-9,23-bis[3-(carbamoylamino)propyl]-12,29-bis[(4-hydroxyphenyl)methyl]-2,5,8,11,14,22,25,28,31-nonaoxo-17,18-dithia-1,4,7,10,13,21,24,27,30-nonazabicyclo[30.3.0]pentatriacontane-20-carboxamide

InChi Key

DGQKRQOCJFODHN-BEJJTRLSSA-N

InChi Code

InChI=1S/C90H141N33O18S2/c91-35-5-3-17-59-75(130)117-64(18-4-6-36-92)84(139)123-43-13-24-70(123)83(138)120-66(46-51-28-33-56(125)34-29-51)79(134)116-61(21-10-40-108-88(101)102)74(129)114-63(23-12-42-110-90(104)141)77(132)121-68(81(136)111-58(71(94)126)19-8-38-106-86(97)98)48-142-143-49-69(82(137)119-65(45-50-26-31-55(124)32-27-50)78(133)115-62(73(128)113-59)22-11-41-109-89(103)140)122-80(135)67(47-52-25-30-53-14-1-2-15-54(53)44-52)118-76(131)60(20-9-39-107-87(99)100)112-72(127)57(93)16-7-37-105-85(95)96/h1-2,14-15,25-34,44,57-70,124-125H,3-13,16-24,35-43,45-49,91-93H2,(H2,94,126)(H,111,136)(H,112,127)(H,113,128)(H,114,129)(H,115,133)(H,116,134)(H,117,130)(H,118,131)(H,119,137)(H,120,138)(H,121,132)(H,122,135)(H4,95,96,105)(H4,97,98,106)(H4,99,100,107)(H4,101,102,108)(H3,103,109,140)(H3,104,110,141)/t57-,58-,59-,60-,61-,62-,63-,64+,65-,66-,67-,68-,69-,70?/m0/s1

SMILES Code

O=C([C@@H](NC([C@H](CCCNC(N)=O)NC([C@H](CCCNC(N)=N)NC([C@H](CC1=CC=C(O)C=C1)N2)=O)=O)=O)CSSC[C@H](NC([C@@H](NC([C@@H](NC([C@@H](N)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CC3=CC=C4C=CC=CC4=C3)=O)C(N[C@@H](CC5=CC=C(O)C=C5)C(N[C@@H](CCCNC(N)=O)C(N[C@@H](CCCCN)C(N[C@H](CCCCN)C(N6CCCC6C2=O)=O)=O)=O)=O)=O)N[C@@H](CCCNC(N)=N)C(N)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 2,037.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Hennrich U, Seyler L, Schäfer M, Bauder-Wüst U, Eisenhut M, Semmler W, Bäuerle T. Synthesis and in vitro evaluation of 68Ga-DOTA-4-FBn-TN14003, a novel tracer for the imaging of CXCR4 expression. Bioorg Med Chem. 2012 Feb 15;20(4):1502-10. doi: 10.1016/j.bmc.2011.12.052. Epub 2012 Jan 2. PubMed PMID: 22264762. 2: George GP, Stevens E, Åberg O, Nguyen QD, Pisaneschi F, Spivey AC, Aboagye EO. Preclinical evaluation of a CXCR4-specific (68)Ga-labelled TN14003 derivative for cancer PET imaging. Bioorg Med Chem. 2014 Jan 15;22(2):796-803. doi: 10.1016/j.bmc.2013.12.012. Epub 2013 Dec 11. PubMed PMID: 24365390. 3: Abraham M, Biyder K, Begin M, Wald H, Weiss ID, Galun E, Nagler A, Peled A. Enhanced unique pattern of hematopoietic cell mobilization induced by the CXCR4 antagonist 4F-benzoyl-TN14003. Stem Cells. 2007 Sep;25(9):2158-66. Epub 2007 May 24. PubMed PMID: 17525235. 4: Abraham M, Beider K, Wald H, Weiss ID, Zipori D, Galun E, Nagler A, Eizenberg O, Peled A. The CXCR4 antagonist 4F-benzoyl-TN14003 stimulates the recovery of the bone marrow after transplantation. Leukemia. 2009 Aug;23(8):1378-88. doi: 10.1038/leu.2009.56. Epub 2009 Mar 26. PubMed PMID: 19322207. 5: Beider K, Begin M, Abraham M, Wald H, Weiss ID, Wald O, Pikarsky E, Zeira E, Eizenberg O, Galun E, Hardan I, Engelhard D, Nagler A, Peled A. CXCR4 antagonist 4F-benzoyl-TN14003 inhibits leukemia and multiple myeloma tumor growth. Exp Hematol. 2011 Mar;39(3):282-92. doi: 10.1016/j.exphem.2010.11.010. Epub 2010 Dec 5. PubMed PMID: 21138752. 6: Jia D, Li Y, Han R, Wang K, Cai G, He C, Yang L. miR 146a 5p expression is upregulated by the CXCR4 antagonist TN14003 and attenuates SDF 1 induced cartilage degradation. Mol Med Rep. 2019 May;19(5):4388-4400. doi: 10.3892/mmr.2019.10076. Epub 2019 Mar 21. PubMed PMID: 30942441; PubMed Central PMCID: PMC6472139. 7: Lefort S, Thuleau A, Kieffer Y, Sirven P, Bieche I, Marangoni E, Vincent-Salomon A, Mechta-Grigoriou F. CXCR4 inhibitors could benefit to HER2 but not to triple-negative breast cancer patients. Oncogene. 2017 Mar 2;36(9):1211-1222. doi: 10.1038/onc.2016.284. Epub 2016 Sep 26. PubMed PMID: 27669438; PubMed Central PMCID: PMC5340801. 8: Nedev H, Saragovi HU. Synthesis of biotinyl-TN14003, anti-HIV peptide amide. Adv Exp Med Biol. 2009;611:155-6. PubMed PMID: 19400137. 9: Bai R, Liang Z, Yoon Y, Liu S, Gaines T, Oum Y, Shi Q, Mooring SR, Shim H. Symmetrical bis-tertiary amines as novel CXCR4 inhibitors. Eur J Med Chem. 2016 Aug 8;118:340-50. doi: 10.1016/j.ejmech.2016.04.040. Epub 2016 Apr 19. PubMed PMID: 27179215; PubMed Central PMCID: PMC4894032. 10: Mori T, Doi R, Koizumi M, Toyoda E, Ito D, Kami K, Masui T, Fujimoto K, Tamamura H, Hiramatsu K, Fujii N, Imamura M. CXCR4 antagonist inhibits stromal cell-derived factor 1-induced migration and invasion of human pancreatic cancer. Mol Cancer Ther. 2004 Jan;3(1):29-37. PubMed PMID: 14749473. 11: Di Cesare S, Marshall JC, Fernandes BF, Logan P, Antecka E, Filho VB, Burnier MN Jr. In vitro characterization and inhibition of the CXCR4/CXCL12 chemokine axis in human uveal melanoma cell lines. Cancer Cell Int. 2007 Nov 14;7:17. PubMed PMID: 18001467; PubMed Central PMCID: PMC2194662. 12: Taromi S, Kayser G, Catusse J, von Elverfeldt D, Reichardt W, Braun F, Weber WA, Zeiser R, Burger M. CXCR4 antagonists suppress small cell lung cancer progression. Oncotarget. 2016 Dec 20;7(51):85185-85195. doi: 10.18632/oncotarget.13238. PubMed PMID: 27835905; PubMed Central PMCID: PMC5356728. 13: Leung K. (64)Cu-1,4,7-Triazacyclononane-1,4,7-triacetic acid-Arg-Arg-Natl-Cys-Tyr-Cit-Lys-d-Lys-Pro-Tyr-Arg-Cit-Cys-Arg-NH(2). 2011 Nov 15 [updated 2012 Feb 9]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK84037/ PubMed PMID: 22338192. 14: Leung K. (64)Cu-1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid-Arg-Arg-Natl-Cys-Tyr-Cit-Lys-d-Lys-Pro-Tyr-Arg-Cit-Cys-Arg-NH(2). 2011 Nov 15 [updated 2012 Feb 9]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK84043/ PubMed PMID: 22338195. 15: Burger JA, Stewart DJ, Wald O, Peled A. Potential of CXCR4 antagonists for the treatment of metastatic lung cancer. Expert Rev Anticancer Ther. 2011 Apr;11(4):621-30. doi: 10.1586/era.11.11. Review. PubMed PMID: 21504328. 16: Burger JA, Stewart DJ. CXCR4 chemokine receptor antagonists: perspectives in SCLC. Expert Opin Investig Drugs. 2009 Apr;18(4):481-90. doi: 10.1517/13543780902804249 . Review. PubMed PMID: 19335276. 17: De Clercq E. Recent advances on the use of the CXCR4 antagonist plerixafor (AMD3100, Mozobil™) and potential of other CXCR4 antagonists as stem cell mobilizers. Pharmacol Ther. 2010 Dec;128(3):509-18. doi: 10.1016/j.pharmthera.2010.08.009. Epub 2010 Sep 15. Review. PubMed PMID: 20826182. 18: Masyuk M, Abduelmula A, Morosan-Puopolo G, Ödemis V, Rehimi R, Khalida N, Yusuf F, Engele J, Tamamura H, Theiss C, Brand-Saberi B. Retrograde migration of pectoral girdle muscle precursors depends on CXCR4/SDF-1 signaling. Histochem Cell Biol. 2014 Nov;142(5):473-88. doi: 10.1007/s00418-014-1237-7. Epub 2014 Jun 28. PubMed PMID: 24972797. 19: Menu E, Asosingh K, Indraccolo S, De Raeve H, Van Riet I, Van Valckenborgh E, Vande Broek I, Fujii N, Tamamura H, Van Camp B, Vanderkerken K. The involvement of stromal derived factor 1alpha in homing and progression of multiple myeloma in the 5TMM model. Haematologica. 2006 May;91(5):605-12. Epub 2006 Apr 19. Erratum in: Haematologica. 2007 Nov;92(11):1584. Van de Broek, Isabelle [corrected to Vande Broek, Isabelle]. PubMed PMID: 16627256. 20: Peled A, Abraham M, Avivi I, Rowe JM, Beider K, Wald H, Tiomkin L, Ribakovsky L, Riback Y, Ramati Y, Aviel S, Galun E, Shaw HL, Eizenberg O, Hardan I, Shimoni A, Nagler A. The high-affinity CXCR4 antagonist BKT140 is safe and induces a robust mobilization of human CD34+ cells in patients with multiple myeloma. Clin Cancer Res. 2014 Jan 15;20(2):469-79. doi: 10.1158/1078-0432.CCR-13-1302. Epub 2013 Nov 18. PubMed PMID: 24246358.